Dimethylformamide → 2,3-Dimethoxy-6-(10-hydroxydecyl)-4-(2-pyridylmethyloxy)-5-methylphenol hydrochloride

HRID 1648709Notes

Reaction equation

HRID 1648709 reaction equation
C([O:4][C:5]1[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21]C(=O)C)=[C:9]([CH3:25])[C:8]([OH:26])=[C:7]([O:27][CH3:28])[C:6]=1[O:29][CH3:30])(=O)C.Cl.[Cl:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[ClH:32].[CH3:30][O:29][C:6]1[C:7]([O:27][CH3:28])=[C:8]([O:26][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[C:9]([CH3:25])=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[C:5]=1[OH:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 194185331-Acetoxy-6-(10-acetoxydecyl)-2,3-dimethoxy-4-hydroxy-5-methylbenzene

Product 1

HCID 194185202,3-Dimethoxy-6-(10-hydroxydecyl)-4-(2-pyridylmethyloxy)-5-methylphenol hydrochlorideYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-acetoxy-6-(10-acetoxydecyl)-2,3-dimethoxy-4-hydroxy-5-methylbenzene (2.1 g) obtained in Example A-5, 2-chloromethylpyridine hydrochloride (2 g), potassium carbonate (5 g) and dimethylformamide (15 ml) was stirred at room temperature for 16 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was dissolved in methanol (20 ml). Aqueous 1N sodium hydroxide solution (20 ml) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate, and the eluate was concentrated. The residue was dissolved by adding ethanol (30 ml), and conc. hydrochloric acid (0.7 ml) was added. The crystals obtained after concentration under reduced pressure were separated by filtration using ether to obtain the desired compound (1.7 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol (20 ml)
  4. additionAqueous 1N sodium hydroxide solution (20 ml) was added
  5. stirringthe mixture was stirred at room temperature overnight
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. washeluted with ethyl acetate
  8. concentrationthe eluate was concentrated
  9. dissolutionThe residue was dissolved
  10. additionby adding ethanol (30 ml), and conc. hydrochloric acid (0.7 ml)
  11. additionwas added
  12. customThe crystals obtained
  13. concentrationafter concentration under reduced pressure
  14. customwere separated by filtration

Sources & evidence

ORD record
ord-039643b2154e4704b4fbd8b51e2986ec
Source dataset
uspto-grants-1995_07
Patent number
US05436359

Reaction notes

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